Paper colored with sulphonic-acid compounds of dyestuffs obtainable from higher molecular diarylamino-benzoquinones



Patented Mar. 31, 1931 Uni-Tao TA E-s PATENT- OFFICE A :r AND amnion mum 0 or rmxroa'r-or-ma-xam, m me man, or ran-nearon-muam-aocna'r, om, 18819803810 omm mm wom mo,

: e -om-oat-mm-B0m.

or m roux, 1w. 1, a eqnrourron or nmwm rein comm amnoinc noto comma ,or nmrurrs om'anuxnn' raolt mom: 21mm Io Drawing. Application Mejia; as, .15, lei-la! In. 81,11, and la Gamay June 23, I888. The present invention relates topafer colored with a salt of a sulphonic acid 0 a eompound-of the probable general formula v wherein Cl and C, on the one hand and C and C. on the other hand represent carbon atoms belonging to a naphthalene or carbazol nucleus, or to a benzene nucleus which is substituted by at least one eubetitutent of the Igroup consisting of C.H;-O, C,H,-N C.H, -CO--NH-, alkylamino alkyl and halogen.

The obvious] canine-like dyestu'fl'e ebtainable by eating dia/ryluhino-benzoquinones in the presence of whisk-boiling, solvent hevehitherflo-not reached as eul' honic acids on practical" importance for yeing wool an eilk; this is in the fact that these dyestufl'swhieh yieldijfor the moet part red, reddish-brown or 'vielet shades are:

inferior to commercial dyeing-we same tints particularly a! regards their levellin flower.

7 ave found that the sol onic acids of the compounds represented y the above indicated eneral formula are very valuable dyestufis or-coloring aper.

The said compound; are obtainable, for instance, according to the ndin U. S. patent application Ser. No. 8 ,816, 5 ed Ma 18, 1929, from higher molecular diary amino-benzoquinone compounds which may be represented by the fol male:

0 NH-R wherein R means a. naphthalene or carbazol nucleus or a benzene nucleus which is substituted by at least one substit-uent of the group consisting of C.H,O, C.H NH-,

owing general f'ormom group; V

inflict mo! db ar lamixig-dbegi an Emilio com and cite general formula: HAW-R wherein R has the above'indicated meaning and wherein there is at least one free orthoposition injrelationto the NH, group.

When coloring the paper both in the mass and according to the -'ving process beautiful uniform coloratione are obtained being of every good festness to water and light so that ,these lulphonated, probably oxazinel ke condensation roducts'obtaineble from the higher moecular diarylamino-benzoq'umpne hon; unfit constitute a valuable sep- ,ara'teclagsp I fiyestflfls for coloring aper.

Rite f u mn ox'ainplefs erve' to Illustrate ur venhbn it they are ot intended to hunt 1t; thereto, the weight.

1- fl 'peme recur. w i ar v in a, are with water and tn'ii d lwith a iiolution of 1 part of the sodium salt of'the dyeehiif sulphonie acid of the following formula:

w 0 a t v obtained being of a very good fastness to water and light.

2. 100 parts of the paper pulp which have been beaten in e. hollander are diluted with water, mix-ed with a solution of 1 part of the sodium salt of the sulphonatecl benzo-quinone dc rivntive of the following probable formula:

prepared by heat-lug wdi-(betu-rmpl'dhyl'mmino)-dichloro-benzoquinone in nitrobenzene, and then aim! in the usual mauner'wlthiesin soup and sulfate of alumina or, alum, B this operation therein obtained a,beal1jfu uniform violercolorrtion of 1 mrfbl'zim b'ein'g-of a verv godd' fastnessro' wnteriiifl light;

3. I! mixing I00 puts 0t aper pulp which We beenhetten in who node: and diluted by memo! water with ojboliltibn of I purl. o! the sodlllm sllt of the 'slllp'bonated 0xazine-like produchpf tliQfollowlng probable formula:

I o NILCIHI obtoimble by treating 2.5-di-(pi1ra-nmi|iodiphenyla mine} fl-dichloro-Li-benzoquim one with nitrobenzene, And sized in the usual mannerwitl'l resin soap and sulfnleof alumino. By this method a bluish-gray coloration is obtained being of a good fastness to light.

Instead .of the pnra-nmlnmdlphenylamine there may also'be Used the oxazmo-like (lyestufl-sulphonic acids which are obtainable from chloroanil bylreating it with 4-aminolqnelhoxy-diphenylamine, parn-aminu-dimulhyhmiline, para-toluidina mpom-chlornniline. The oxazinelike dyestnll-sulplumit acids which are obtainable from chlomanil by treating it with l-bcnzo 'l'-umino-Jl-mninuhon- 'llollmder and v uted with water" zene or 4-benzoyl-nmino-4'-amino-diphenvlamine also color the paper beautiful tints of good fasthess towaler and light.

Equal beautlfrll coloratiohs of the paper oft-he same fast-mess to water and light are obtained by pa ssiug according to the diving process the final unsized pa erJn known maill?! l li fh a solution of hed'yesfinflfs men t lonerl in he preceding exam les.

Ill we" above given exnmp es and in the claims-hereafter followin we ha-ve given certain chemical iprrpulqa or the dyestuffs to be used according to our invention. However, we want it to be.u. nclorstoollzthlt the chemical reactions involved in the process of preparing theclyestufl's in question are not quite clear. According-to our presentlmowledge the formulae of the dyestufis'as given herein correspond with their chemical properties so that they may.serve as a proper desi nutionof lhe dyestuffs in question.

a claim:

1. Paper colored with a salt of a sulphonic acid of a compound of the probeble general formula:

whereinC and c. on the one hand and c, and C. onthe' other hlndropresent carbon atoms belonging to a. naphthalene or I. carblzol nncleusgor toebenzouo 'nuolegg whichis substitute b. I! leistone so itolml: of the s .11 ,zflnil tlll of Cm, 0.3a -i', '0 w-C NH--., alkylarmne; g-lkyl gand halogen.

2. ,Pa r' c,0lox=od with the sodium salt-of. thesul omc acid compound of the following proba a formula:

having a uniform violet coloration of good fnstness to water and light.

3. Paper colored with the sodium salt of the sulphouic acid compound of the following probable formula:

mm having a uniform blue coloration of good humus; to water and llght.

Ill.

4. Pager colored with the sodium salt'of the sulp onic acid compound of the. following probable formula:

24116.11: I Ol-H Bi l-EN '6 10 having a, bluish-gray coloration of good fastness to 1i ht.

In teshmony wherotif, we aln'x our signatures.

15 GEORG KRAENZLEIN.

.HEINRICH GREUNE.

MAX THIELE. KARL HAGER.

4. Paper colored with the sodium salt of V rho snlphomc ac1d compound of the followmg probable formula:

15 GEORG KRAENZLEIN.

HEINRICH GREUNE.

MAX THIELE. KARL HAGER.

Certificate of Correction Granted Nllll'l'l] 31, 1931, to

GEORG KRAENZLE] N ET AL.

It is hereby certified that error appom's in tho printml spocifionliou of the aboveluunhorod patent requiring corrvction as follows: Pogo 2, lino 5, formula. for Hugroup of characters on the extromo right, for S0 E31 rend 90 371 some pogo, line 25. formula. for the group of ('lmrnctors at lou vr right within llw hravkot for 0.011; rezul (7.6111 and that the said Lottor. Patent should he roml with thPso rorroctions therein that the sumo may conform to the record of the case in the Putont ()flicc.

Signed alul senloll [his 5th do) of May, A. I). 1931.

Patent No. 1,798,544.

LSE.\L.]

M. J. MOORE, lr'fin r Commissioner of Patrmlq'.

Certificate of Corrective Patent No. 1,798,544. Granted .hlillth 31, 1931, w

GEORG KRAENZLEIN J AL.

If is hereby certified that error aplrc'ars in thv printc-d spocificatiun uf lhv abovelllllllblfld patent, requiring correction as fulluws: lngu 2, line 5, formula. for thv group of characters on the extrPmv right, for S0 E31" rend Sfl j'a; same pagv, line 25. formula. for the group of (-hnractm's at Imyvr right within (h1- hrarkel. fur QC H read 0.0.11 and that the said Lottm'z Patent ---h ml(l hv rvml with these mrrections thvrein that the same may (unfm'm tn the record uf the case in the Putvnt ()flicc.

b'igucml and sealed this 5th day of May, A. l). 1931.

[sun] M. .1. MOORE, I vii/1y Uwumirm'oncr of latlmtq. 

